JP2013513617A5 - - Google Patents
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- JP2013513617A5 JP2013513617A5 JP2012543310A JP2012543310A JP2013513617A5 JP 2013513617 A5 JP2013513617 A5 JP 2013513617A5 JP 2012543310 A JP2012543310 A JP 2012543310A JP 2012543310 A JP2012543310 A JP 2012543310A JP 2013513617 A5 JP2013513617 A5 JP 2013513617A5
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- JP
- Japan
- Prior art keywords
- oxo
- carboxamide
- quinoline
- phenyl
- trifluoromethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 4
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- WWNOUYOXHFVZKM-GOSISDBHSA-N (2r)-1-[4-[(4-oxo-1h-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@H]1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O WWNOUYOXHFVZKM-GOSISDBHSA-N 0.000 claims description 2
- WWNOUYOXHFVZKM-SFHVURJKSA-N (2s)-1-[4-[(4-oxo-1h-quinoline-3-carbonyl)amino]-3-(trifluoromethyl)phenyl]pyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O WWNOUYOXHFVZKM-SFHVURJKSA-N 0.000 claims description 2
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 2
- XLQMVHMHVWNGRI-UHFFFAOYSA-N 4-oxo-n-(1,4,4-trimethyl-2,3-dihydroquinolin-7-yl)-1h-quinoline-3-carboxamide Chemical compound C1=CC=C2C(=O)C(C(=O)NC3=CC=C4C(C)(C)CCN(C4=C3)C)=CNC2=C1 XLQMVHMHVWNGRI-UHFFFAOYSA-N 0.000 claims description 2
- XSMLFPTYMLWZDQ-UHFFFAOYSA-N 4-oxo-n-(2-pyridin-2-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC1=CC=CC=C1C1=CC=CC=N1 XSMLFPTYMLWZDQ-UHFFFAOYSA-N 0.000 claims description 2
- QACDVKWZQAJPAB-UHFFFAOYSA-N 4-oxo-n-(3-thiophen-2-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=1)=CC=CC=1C1=CC=CS1 QACDVKWZQAJPAB-UHFFFAOYSA-N 0.000 claims description 2
- CEQMANXOVRMQIY-UHFFFAOYSA-N 4-oxo-n-(4-piperidin-1-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1N1CCCCC1 CEQMANXOVRMQIY-UHFFFAOYSA-N 0.000 claims description 2
- SDNLVYKIJDWLJN-UHFFFAOYSA-N 4-oxo-n-(4-pyridin-3-yloxyphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 SDNLVYKIJDWLJN-UHFFFAOYSA-N 0.000 claims description 2
- DRZXOZNJKLXEFD-UHFFFAOYSA-N 4-oxo-n-(4-pyrrolidin-1-ylphenyl)-1h-quinoline-3-carboxamide Chemical compound C=1NC2=CC=CC=C2C(=O)C=1C(=O)NC(C=C1)=CC=C1N1CCCC1 DRZXOZNJKLXEFD-UHFFFAOYSA-N 0.000 claims description 2
- LSVAGKBGHSEXFA-UHFFFAOYSA-N 4-oxo-n-[2-piperidin-1-yl-4-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=1N1CCCCC1 LSVAGKBGHSEXFA-UHFFFAOYSA-N 0.000 claims description 2
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- NYZFGGHGNAQOOG-UHFFFAOYSA-N 4-oxo-n-[3-piperidin-1-yl-4-(trifluoromethoxy)phenyl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)OC1=CC=C(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)C=C1N1CCCCC1 NYZFGGHGNAQOOG-UHFFFAOYSA-N 0.000 claims description 2
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- QTLUYOQSTSPQBL-UHFFFAOYSA-N 4-oxo-n-[3-pyrrolidin-1-yl-5-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C=1C(C(F)(F)F)=CC(NC(=O)C=2C(C3=CC=CC=C3NC=2)=O)=CC=1N1CCCC1 QTLUYOQSTSPQBL-UHFFFAOYSA-N 0.000 claims description 2
- BPVXFEJJXZTGAV-UHFFFAOYSA-N 4-oxo-n-[4-(4-propan-2-ylpiperazin-1-yl)-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound C1CN(C(C)C)CCN1C(C=C1C(F)(F)F)=CC=C1NC(=O)C1=CNC2=CC=CC=C2C1=O BPVXFEJJXZTGAV-UHFFFAOYSA-N 0.000 claims description 2
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- BDKUNHJMDVNTIK-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-[2-(trifluoromethyl)-1h-indol-6-yl]-1h-quinoline-3-carboxamide Chemical compound C1=C2C=C(C(F)(F)F)NC2=CC(NC(=O)C2=CNC=3C=CC=C(C=3C2=O)O)=C1 BDKUNHJMDVNTIK-UHFFFAOYSA-N 0.000 claims description 2
- SOWGYRWNIPNSAO-UHFFFAOYSA-N 5-hydroxy-4-oxo-n-[4-propan-2-yl-2-(trifluoromethyl)phenyl]-1h-quinoline-3-carboxamide Chemical compound FC(F)(F)C1=CC(C(C)C)=CC=C1NC(=O)C1=CNC2=CC=CC(O)=C2C1=O SOWGYRWNIPNSAO-UHFFFAOYSA-N 0.000 claims description 2
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Families Citing this family (145)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA200602755B (en) | 2003-09-06 | 2007-06-27 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
| JP4869072B2 (ja) * | 2003-11-14 | 2012-02-01 | バーテックス ファーマシューティカルズ インコーポレイテッド | Atp結合カセットトランスポーターのモジュレーターとして有用なチアゾールおよびオキサゾール |
| US7977322B2 (en) | 2004-08-20 | 2011-07-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| NZ587549A (en) * | 2004-06-24 | 2012-10-26 | Vertex Pharma | 6-Amino-indole derivatives and processes for their preparation |
| US20140343098A1 (en) * | 2004-06-24 | 2014-11-20 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| US8354427B2 (en) * | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| EP1912983B1 (en) | 2005-08-11 | 2011-06-08 | Vertex Pharmaceuticals, Inc. | Modulators of cystic fibrosis transmembrane conductance regulator |
| KR101331768B1 (ko) * | 2005-11-08 | 2013-11-22 | 버텍스 파마슈티칼스 인코포레이티드 | Atp 결합 카세트 수송체의 헤테로사이클릭 조정제 |
| EP1974212A1 (en) * | 2005-12-27 | 2008-10-01 | Vertex Pharmaceuticals Incorporated | Compounds useful in cftr assays and methods therewith |
| US7671221B2 (en) * | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| CA2635581C (en) | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| CA2856037C (en) * | 2005-12-28 | 2017-03-07 | Vertex Pharmaceuticals Incorporated | Modulators of atp-binding cassette transporters |
| US10022352B2 (en) | 2006-04-07 | 2018-07-17 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| PL2674428T3 (pl) | 2006-04-07 | 2017-01-31 | Vertex Pharmaceuticals Incorporated | Modulatory transporterów z kasetą wiążącą ATP |
| US7645789B2 (en) * | 2006-04-07 | 2010-01-12 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| CA2686838C (en) | 2007-05-09 | 2017-03-14 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
| US20110177999A1 (en) * | 2007-08-09 | 2011-07-21 | Vertex Pharmaceuticals Incorporated | Therapeutic Combinations Useful in Treating CFTR Related Diseases |
| AU2008302598B2 (en) | 2007-08-24 | 2014-07-17 | Vertex Pharmaceuticals Incorporated | Isothiazolopyridinones useful for the treatment of (inter alia) Cystic Fibrosis |
| WO2009049159A1 (en) | 2007-10-10 | 2009-04-16 | Parion Sciences, Inc. | Delivering osmolytes by nasal cannula |
| SI2578571T1 (sl) | 2007-11-16 | 2016-01-29 | Vertex Pharmaceuticals Incorporated | Izokinolinski modulatorji prenašalcev z atp-vezavno kaseto |
| US20100036130A1 (en) | 2007-12-07 | 2010-02-11 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
| HRP20170241T2 (hr) | 2007-12-07 | 2023-03-17 | Vertex Pharmaceuticals Incorporated | Čvrsti oblici 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il)ciklopropankarboksamido)-3-metilpiridin-2-il)benzojeve kiseline |
| AU2008335439A1 (en) * | 2007-12-07 | 2009-06-18 | Vertex Pharmaceuticals Incorporated | Formulations of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| DK2639223T3 (en) | 2007-12-07 | 2017-06-19 | Vertex Pharma | Process for Preparation of Cycloalkylcarboxiamido-pyridine Benzoic Acids |
| NZ736561A (en) | 2008-02-28 | 2018-02-23 | Vertex Pharma | Heteroaryl derivatives as cftr modulators |
| DK2615085T3 (en) | 2008-03-31 | 2015-10-05 | Vertex Pharma | Pyridyl derivatives as CFTR modulators |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| US8716338B2 (en) * | 2008-09-29 | 2014-05-06 | Vertex Pharmaceuticals Incorporated | Dosage units of 3-(6-(1-(2,2-difluorobenzo[D] [1,3] dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid |
| UA104601C2 (uk) * | 2008-10-23 | 2014-02-25 | Вертекс Фармасьютікалз, Інкорпорейтед | Модулятори регулятора трансмембранної провідності при муковісцидозі |
| PL2408750T3 (pl) | 2009-03-20 | 2016-02-29 | Vertex Pharma | Sposób otrzymywania modulatorów błonowego regulatora przewodnictwa swoistego dla mukowiscydozy |
| AU2010310449A1 (en) | 2009-10-22 | 2012-05-03 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
| DK3150198T3 (da) | 2010-04-07 | 2021-11-01 | Vertex Pharma | Farmaceutiske sammensætninger af 3-(6-(1-(2,2-difluorbenzo[d][1,3]dioxol-5-yl)-cyclopropancarboxamido)-3-methylpyriodin-2-yl)benzoesyre og indgivelse deraf |
| RS54783B1 (sr) | 2010-04-07 | 2016-10-31 | Vertex Pharma | Čvrste forme 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il)ciklopropankarboksiamido)-3-metilpiridin-2-il)benzoeve kiseline |
| CA2797118C (en) | 2010-04-22 | 2021-03-30 | Vertex Pharmaceuticals Incorporated | Process of producing cycloalkylcarboxamido-indole compounds |
| WO2011133953A1 (en) | 2010-04-22 | 2011-10-27 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions and administrations thereof |
| NZ603042A (en) | 2010-04-22 | 2015-02-27 | Vertex Pharma | Pharmaceutical compositions comprising cftr modulators and administrations thereof |
| EP2575814A1 (en) * | 2010-05-20 | 2013-04-10 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions and administrations thereof |
| US20130210883A1 (en) | 2010-05-21 | 2013-08-15 | Johannes Grillari | Lipase inhibitors |
| CA2800018C (en) | 2010-05-21 | 2021-09-28 | Universitaet Fuer Bodenkultur Wien | Compositions for use in treating or diagnosing bone disorders and/or cardiovascular disorders |
| US8563593B2 (en) | 2010-06-08 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Formulations of (R)-1-(2,2-difluorobenzo[D] [1,3] dioxol-5-yl)-N-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1H-indol-5-yl)cyclopropanecarboxamide |
| WO2012061926A1 (en) * | 2010-11-08 | 2012-05-18 | Zalicus Pharmaceuticals Ltd. | Bisarylsulfone and dialkylarylsulfone compounds as calcium channel blockers |
| US8802700B2 (en) * | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| HUE047354T2 (hu) | 2011-05-18 | 2020-04-28 | Vertex Pharmaceuticals Europe Ltd | Ivacaftor deuterizált származékai |
| EP2717855A4 (en) | 2011-06-07 | 2014-11-12 | Parion Sciences Inc | PROCESSING METHODS |
| US8945605B2 (en) | 2011-06-07 | 2015-02-03 | Parion Sciences, Inc. | Aerosol delivery systems, compositions and methods |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
| MX357328B (es) | 2011-11-08 | 2018-07-05 | Vertex Pharma | Moduladores de trasportadores de casete enlazante de atp. |
| AU2013226076B2 (en) | 2012-02-27 | 2017-11-16 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administration thereof |
| US8674108B2 (en) | 2012-04-20 | 2014-03-18 | Vertex Pharmaceuticals Incorporated | Solid forms of N-[2,4-bis(1,1-dimethylethy)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| LT2855435T (lt) | 2012-05-29 | 2018-09-10 | Parion Sciences, Inc. | Amino amidai, panašūs į dendrimerus, su natrio kanalų blokavimo aktyvumu, skirti gydyti sausų akių sindromą ir kitas gleivinių ligas |
| EP2872122A1 (en) | 2012-07-16 | 2015-05-20 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of (r)-1-(2,2-diflurorbenzo[d][1,3]dioxol-5-yl)-n-(1-(2,3-dihydroxypropyl)-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)-1h-indol-5-yl) cyclopropanecarboxamide and administration thereof |
| WO2014099673A1 (en) | 2012-12-17 | 2014-06-26 | Parion Sciences, Inc. | 3,5-diamino-6-chloro-n-(n-(4-phenylbutyl)carbamimidoyl) pyrazine-2- carboxamide compounds |
| US9593084B2 (en) | 2012-12-17 | 2017-03-14 | Parion Sciences, Inc. | Chloro-pyrazine carboxamide derivatives with epithelial sodium channel blocking activity |
| ES2674665T3 (es) | 2012-12-17 | 2018-07-03 | Parion Sciences, Inc. | Compuestos de 3,5-diamino-6-cloro-N-(N-(4-fenilbutilo)carbamimidoilo)-pirazina-2-carboxamida |
| EP3263559A1 (en) * | 2013-01-22 | 2018-01-03 | Technische Universität Graz | Lipase inhibitors |
| CN103224466A (zh) * | 2013-04-15 | 2013-07-31 | 北京大学 | 具有β-分泌酶抑制功能的化合物及其制备方法与应用 |
| RU2718044C2 (ru) | 2013-11-12 | 2020-03-30 | Вертекс Фармасьютикалз Инкорпорейтед | Способ получения фармацевтических композиций для лечения опосредованных cftr заболеваний |
| RS62140B1 (sr) | 2014-04-15 | 2021-08-31 | Vertex Pharma | Farmaceutske kompozicije za lečenje bolesti posredovanih transmembranskim regulatorom provodljivosti cistične fibroze |
| KR101905295B1 (ko) | 2014-06-03 | 2018-10-05 | 노파르티스 아게 | 나프티리딘디온 유도체 |
| AR101198A1 (es) | 2014-07-16 | 2016-11-30 | Gruenenthal Gmbh | Pirimidinas 2,5-sustituidas como inhibidores de pde4b |
| AR101196A1 (es) | 2014-07-16 | 2016-11-30 | Gruenenthal Gmbh | Compuestos de pirimidina sustituidos |
| GB201415381D0 (en) | 2014-08-29 | 2014-10-15 | Algipharma As | Inhalable powder formulations of alginate oligomers |
| US20200347038A1 (en) | 2014-08-29 | 2020-11-05 | Russell Dahl | Quinolines that modulate serca and their use for treating disease |
| EP3193939A4 (en) * | 2014-09-17 | 2018-10-24 | The Regents of The University of California | Small lipopeptidomimetic inhibitors of ghrelin o-acyl transferase |
| CA2963640A1 (en) | 2014-10-06 | 2016-04-14 | Flatley Discovery Lab, Llc | Triazolopyridine compounds and methods for the treatment of cystic fibrosis |
| IL313498A (en) | 2014-10-06 | 2024-08-01 | Vertex Pharma | Modulators of the cystic fibrosis transmembrane conductance regulator |
| KR20170063954A (ko) | 2014-10-07 | 2017-06-08 | 버텍스 파마슈티칼스 인코포레이티드 | 낭성 섬유증 막횡단 전도도 조절자의 조정제의 공-결정 |
| WO2016057811A1 (en) * | 2014-10-08 | 2016-04-14 | Nivalis Therapeutics, Inc. | Methods for the treatment of cystic fibrosis |
| MX2017005663A (es) | 2014-10-31 | 2018-03-01 | Abbvie Sarl | Tetrahidropiranos sustituidos y metodo de uso. |
| HRP20211194T1 (hr) | 2014-11-18 | 2021-10-29 | Vertex Pharmaceuticals Inc. | Postupak za provođenje testova velike propusnosti putem tekućinske kromatografije visoke djelotvornosti |
| US9382208B1 (en) | 2015-01-26 | 2016-07-05 | Vanderbilt University | Negative allosteric modulators of metabotropic glutamate receptor 2 |
| AU2016219231B2 (en) | 2015-02-11 | 2020-08-20 | Icahn School Of Medicine At Mount Sinai | Benzenesulfonamide upregulators of NPC1 for neimann-pick disease and other lysosomal storage disorders |
| GB201504878D0 (en) | 2015-03-23 | 2015-05-06 | Algipharma As | Use of alginate oligomers and CFTR modulators in the treatment of conditions associated with CFTR dysfuntion |
| BR112017026132A2 (pt) | 2015-06-02 | 2018-08-28 | AbbVie S.à.r.l. | piridinas substituídas e métodos de uso |
| US9840513B2 (en) | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| CN106467541B (zh) * | 2015-08-18 | 2019-04-05 | 暨南大学 | 取代喹诺酮类衍生物或其药学上可接受的盐或立体异构体及其药用组合物和应用 |
| HK1258473A1 (zh) | 2015-09-25 | 2019-11-15 | Vertex Pharmaceuticals (Europe) Limited | 氘代cftr增效剂 |
| GB201517639D0 (en) | 2015-10-06 | 2015-11-18 | Algipharma As | Use of alginate oligomers to treat or prevent microbial overgrowth in the intestinal tract |
| US10130622B2 (en) | 2015-10-09 | 2018-11-20 | Abbvie S.Á.R.L. | Compounds for treatment of cystic fibrosis |
| EP3359539A1 (en) | 2015-10-09 | 2018-08-15 | AbbVie S.À.R.L. | Substituted pyrazolo[3,4-b]pyridin-6-carboxylic acids and their use |
| WO2017060874A1 (en) | 2015-10-09 | 2017-04-13 | Abbvie S.Á.R.L | N-sulfonylated pyrazolo[3,4-b]pyridin-6-carboxamides and method of use |
| HUP1600270A2 (hu) | 2016-04-25 | 2017-10-30 | Druggability Tech Ip Holdco Ltd | Ivacaftornak, sóinak és származékainak komplexei, eljárás azok elõállítására és azok gyógyszerészetileg elfogadott készítményei |
| US10206915B2 (en) | 2016-04-25 | 2019-02-19 | Druggability Technologies Ip Holdco Limited | Complexes of Ivacaftor and its salts and derivatives, process for the preparation thereof and pharmaceutical compositions containing them |
| US10383865B2 (en) | 2016-04-25 | 2019-08-20 | Druggability Technologies Ip Holdco Limited | Pharmaceutical combination composition comprising complex formulations of Ivacaftor and Lumacaftor and their salts and derivatives, process for their preparation thereof and pharmaceutical compositions containing them |
| HUP1600271A2 (hu) | 2016-04-25 | 2017-10-30 | Druggability Tech Ip Holdco Ltd | Ivacaftor és Lumacaftor sóinak és származékainak komplexei, eljárás azok elõállítására és azok gyógyszerészetileg elfogadható készítményei |
| EP3448842A1 (en) | 2016-04-26 | 2019-03-06 | AbbVie S.À.R.L. | Modulators of cystic fibrosis transmembrane conductance regulator protein |
| US10138227B2 (en) | 2016-06-03 | 2018-11-27 | Abbvie S.Á.R.L. | Heteroaryl substituted pyridines and methods of use |
| CN106366002B (zh) * | 2016-08-30 | 2019-01-22 | 京博农化科技股份有限公司 | 一种啶酰菌胺中间体4′-氯-2-氨基联苯的合成方法 |
| HRP20211683T1 (hr) | 2016-09-30 | 2022-03-04 | Vertex Pharmaceuticals Incorporated | Modulator transmembranskog regulatora provodljivosti cistične fibroze, farmaceutski pripravci, postupci liječenja, i postupak za pripravu modulatora |
| US9981910B2 (en) * | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| MX2021013639A (es) | 2016-12-09 | 2022-09-30 | Vertex Pharma | Forma cristalina del compuesto 1, un modulador del regulador de conductancia transmembrana de fibrosis quística, procesos para su preparación, composiciones farmacéuticas del compuesto 1, y su uso en el tratamiento de fibrosis quística. |
| WO2018116185A1 (en) | 2016-12-20 | 2018-06-28 | AbbVie S.à.r.l. | Deuterated cftr modulators and methods of use |
| TW201831471A (zh) | 2017-02-24 | 2018-09-01 | 盧森堡商艾伯維公司 | 囊腫纖化症跨膜傳導調節蛋白的調節劑及其使用方法 |
| AU2018279646B2 (en) | 2017-06-08 | 2023-04-06 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| AU2018304168B2 (en) | 2017-07-17 | 2023-05-04 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| TWI799435B (zh) | 2017-08-02 | 2023-04-21 | 美商維泰克斯製藥公司 | 製備化合物之製程 |
| CA3108484A1 (en) | 2017-08-04 | 2019-02-07 | Anthony Stewart Campbell | Inhibitors of microbially induced amyloid |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2019079760A1 (en) | 2017-10-19 | 2019-04-25 | Vertex Pharmaceuticals Incorporated | CRYSTALLINE FORMS AND COMPOSITIONS OF CFTR MODULATORS |
| IL305169B2 (en) * | 2017-12-01 | 2025-07-01 | Vertex Pharma | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| US11465985B2 (en) | 2017-12-08 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| TWI810243B (zh) | 2018-02-05 | 2023-08-01 | 美商維泰克斯製藥公司 | 用於治療囊腫纖化症之醫藥組合物 |
| LT3752510T (lt) | 2018-02-15 | 2023-04-11 | Vertex Pharmaceuticals Incorporated | Makrocikliniai junginiai kaip cistinės fibrozės transmembraninio laidumo reguliatoriaus moduliatoriai, jų farmacinės kompozicijos, jų panaudojimas cistinės fibrozės gydymui ir jų gamybos būdas |
| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
| WO2019200246A1 (en) | 2018-04-13 | 2019-10-17 | Alexander Russell Abela | Modulators of cystic fibrosis transmembrane conductance regulator, pharmaceutical compositions, methods of treatment, and process for making the modulator |
| JP7349491B2 (ja) * | 2018-07-12 | 2023-09-22 | ユーシービー バイオファルマ エスアールエル | Il-17モジュレーターとしてのスピロ環状インダン類似体 |
| WO2020158870A1 (ja) * | 2019-01-30 | 2020-08-06 | 学校法人慶應義塾 | パーキンソン病治療薬 |
| UY38630A (es) | 2019-04-03 | 2020-10-30 | Vertex Pharma | Agentes moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US12303502B2 (en) | 2019-04-18 | 2025-05-20 | Kinedexe UK Limited | Oral liquid composition comprising ivacaftor |
| US11345691B2 (en) | 2019-06-03 | 2022-05-31 | AbbVie Global Enterprises Ltd. | Prodrug modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| US11236067B2 (en) | 2019-07-12 | 2022-02-01 | Orphomed, Inc. | Compound for treating cystic fibrosis |
| EP4013760A1 (en) | 2019-08-14 | 2022-06-22 | Vertex Pharmaceuticals Incorporated | Crystalline forms of cftr modulators |
| US11584761B2 (en) | 2019-08-14 | 2023-02-21 | Vertex Pharmaceuticals Incorporated | Process of making CFTR modulators |
| TWI867024B (zh) | 2019-08-14 | 2024-12-21 | 美商維泰克斯製藥公司 | 囊腫纖維化跨膜傳導調節蛋白之調節劑 |
| IL292965A (en) | 2019-11-12 | 2022-07-01 | Genzyme Corp | 6-membered heteroarylaminosulfonamides and methods of use |
| JP2023503470A (ja) * | 2019-11-25 | 2023-01-30 | ゲイン セラピューティクス エスアー | ガラクトセレブロシダーゼの活性の変質に関連する状態におけるアリールおよびヘテロアリール化合物、ならびにそれらの治療的使用 |
| WO2021113809A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| WO2021113806A1 (en) | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| ES3037292T3 (en) | 2019-12-11 | 2025-09-30 | Taro Pharma Ind | Preparation of trifarotene and intermediates and polymorphs thereof |
| CN113831301B (zh) * | 2020-06-08 | 2023-06-06 | 沈阳药科大学 | 苯并噻唑类衍生物及其用途 |
| US11730729B2 (en) | 2020-07-20 | 2023-08-22 | Neurodon Corporation | Quinolines that modulate SERCA and their use for treating disease |
| CR20230120A (es) | 2020-08-07 | 2023-09-01 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US12324802B2 (en) | 2020-11-18 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| AU2021397294A1 (en) | 2020-12-10 | 2023-07-06 | Vertex Pharmaceuticals Incorporated | Methods of treatment for cystic fibrosis |
| EP4274828A1 (en) | 2021-01-06 | 2023-11-15 | AbbVie Global Enterprises Ltd. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| US20220213041A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| CN113149881B (zh) * | 2021-03-04 | 2022-07-19 | 宁波大学 | 一种手性衍生化试剂及其制备方法和应用 |
| EP4396176A1 (en) | 2021-09-03 | 2024-07-10 | Genzyme Corporation | Indole compounds and uses thereof in the treatement of cystic fibrosis |
| EP4396179A1 (en) | 2021-09-03 | 2024-07-10 | Genzyme Corporation | Indole compounds and methods of use |
| CN114085197B (zh) * | 2021-12-01 | 2024-03-29 | 合肥创新医药技术有限公司 | 4-(3-三氟甲基苯基)-1-哌嗪-乙醇、氟班色林中间体、氟班色林的合成方法 |
| WO2024054851A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocyclic compounds, compositions and methods of using thereof |
| WO2024054845A1 (en) | 2022-09-07 | 2024-03-14 | Sionna Therapeutics | Macrocycic compounds, compositions, and methods of using thereof |
| AU2023338225A1 (en) | 2022-09-07 | 2025-03-20 | Genzyme Corporation | Macrocyclic compounds, compositions, and methods of using thereof |
| CN119894906A (zh) | 2022-09-15 | 2025-04-25 | 爱杜西亚药品有限公司 | 大环cftr调节剂 |
| CN119907667A (zh) | 2022-09-15 | 2025-04-29 | 爱杜西亚药品有限公司 | 大环cftr调节剂与cftr校正剂和/或cftr增效剂的组合 |
| CN116082163B (zh) * | 2023-01-06 | 2023-10-13 | 河北凡克新材料有限公司 | 一种3’,4’-二氟-2’-胺基联苯的制备方法 |
| CN116410180B (zh) * | 2023-03-01 | 2024-09-10 | 青岛大学 | 4-氧代喹啉-3-甲酰胺衍生物及其应用 |
| WO2025132358A1 (en) | 2023-12-21 | 2025-06-26 | Galapagos Nv | Novel compounds and pharmaceutical compositions thereof for the treatment of infectious diseases |
| WO2025186214A1 (en) | 2024-03-05 | 2025-09-12 | Idorsia Pharmaceuticals Ltd | Macrocyclic cftr modulators |
| CN119528747B (zh) * | 2025-01-23 | 2025-05-13 | 烟台泰和新材高分子新材料研究院有限公司 | 一种3,4’-二氨基二苯醚的制备方法 |
Family Cites Families (133)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5874424A (en) | 1995-12-20 | 1999-02-23 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β converting enzyme |
| US3524858A (en) | 1967-05-18 | 1970-08-18 | Warner Lambert Pharmaceutical | 1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid |
| BE757639A (fr) | 1969-10-17 | 1971-04-16 | Roussel Uclaf | Nouveaux derives de la cephalosporine et procede de preparation |
| GB1433774A (en) | 1973-02-26 | 1976-04-28 | Allen & Hanburys Ltd | Heterocyclic compounds apparatus for conveying articles |
| GB1433151A (en) | 1973-04-05 | 1976-04-22 | Allen & Hanburys Ltd | Benzo-ij-quinolizines |
| FR2281761A1 (fr) | 1974-08-13 | 1976-03-12 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2324304A2 (fr) | 1975-09-22 | 1977-04-15 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2340092A2 (fr) | 1976-02-09 | 1977-09-02 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| FR2340735A1 (fr) * | 1976-02-11 | 1977-09-09 | Roussel Uclaf | Nouveaux derives de l'acide 3-quinoleine carboxylique, leur procede de preparation et leur application comme medicament |
| US4312870A (en) | 1979-06-21 | 1982-01-26 | Ciba-Geigy Corporation | Pyrazoloquinolines |
| HU190796B (en) | 1981-06-12 | 1986-11-28 | Roussel Uclaf,Fr | Process for producing n-dihydrothiazolyl-3-quinoline-carboxamide derivatives |
| FR2509728A1 (fr) | 1981-07-17 | 1983-01-21 | Roussel Uclaf | Nouveaux derives de la quinoleine, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant |
| FR2537140B1 (fr) | 1982-12-07 | 1986-07-18 | Roussel Uclaf | Nouveaux derives de la 4-hydroxy-3-quinoleine carboxamide, leur sels, procede de preparation, application a titre de medicaments, et compositions les renfermant |
| SU1360584A3 (ru) * | 1983-08-12 | 1987-12-15 | Варнер-Ламберт Компани (Фирма) | Способ получени нафтиридинхинолин-или бензоксазинкарбоновых кислот или их фармацевтически допустимых солей присоединени кислоты |
| US4845105A (en) | 1984-10-30 | 1989-07-04 | Roussel Uclaf | 4-OH-quinoline carboxylic acid amides having analgesic and anti-inflammatory activity |
| US4687539A (en) | 1986-10-29 | 1987-08-18 | International Business Machines Corp. | End point detection and control of laser induced dry chemical etching |
| DE3702393A1 (de) | 1987-01-28 | 1988-08-11 | Bayer Ag | 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo- 3-chinolincarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende antibakterielle mittel |
| DD279887A1 (de) | 1987-07-03 | 1990-06-20 | Inst Pharmakologische Forschun | Verfahren zur herstellung von d-alpha-(4(1h)-1,5-naphthyridon-3-carboxamido)-benzylpenicillin und anderen beta-lactamantibiotika |
| US4777252A (en) | 1987-08-13 | 1988-10-11 | E. R. Squibb & Sons, Inc. | 2-oxo-1-[[(substituted sulfonyl)amino]-carbonyl]azetidines |
| DE3827253A1 (de) | 1987-08-20 | 1989-03-02 | Sandoz Ag | Ester und amide von cyclischen carbonsaeuren und cyclischen alkoholen und aminen sowie verfahren zu deren herstellung und sie enthaltende therapeutische zusammensetzungen |
| DE3731516A1 (de) | 1987-09-18 | 1989-03-30 | Bayer Ag | N-aryl-stickstoffheterocyclen |
| DE3811341A1 (de) | 1987-10-09 | 1989-04-27 | Bayer Ag | In 7-stellung c-verknuepfte chinolon- und 1,8-naphthyridin-4-on-carbonsaeure und ein verfahren zu ihrer herstellung |
| US4786644A (en) | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
| DE3808118A1 (de) | 1988-03-11 | 1989-09-21 | Bayer Ag | Verfahren zur herstellung von 1-cyclopropyl-chinoloncarbonsaeuren und deren derivaten |
| DE3808117A1 (de) | 1988-03-11 | 1989-09-21 | Bayer Ag | N-cyclopropylaniline und deren verwendung in verfahren zur herstellung von 1-cyclopropyl-chinoloncarbonsaeuren und deren derivaten |
| DE3816119A1 (de) | 1988-05-11 | 1989-11-23 | Bayer Ag | 7-substituierte chinolon- und naphthyridoncarbonsaeure-derivate |
| DK273689A (da) | 1988-06-06 | 1989-12-07 | Sanofi Sa | 4-amino-3-carboxyquinoliner og -naphthyridiner, fremgangsmaade til deres fremstilling og anvendelse deraf i laegemidler |
| DE3827221A1 (de) | 1988-08-11 | 1990-02-15 | Bayer Ag | Substituierte n-phenyl-stickstoff- bzw. stickstoff-schwefel-heterocyclen, verfahren sowie entsprechende heterocyclische phenolderivate, phenyliso(thio)cyanate und -carbamate als zwischenprodukte zu ihrer herstellung, ihre verwendung in herbiziden und pflanzenwuchsregulierenden mitteln |
| US5491139A (en) | 1988-10-24 | 1996-02-13 | The Procter & Gamble Company | Antimicrobial quinolonyl lactams |
| LU87611A1 (fr) | 1989-10-20 | 1991-05-07 | Oreal | Composition tinctoriale pour fibres keratiniques contenant des precurseurs de colorants par oxydation et des coupleurs amino indoliques,procedes de teinture mettant en oeuvre ces compositions et composes nouveaux |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| FR2662713B1 (fr) | 1990-05-29 | 1994-04-08 | Oreal | Procede de teinture de fibres keratiniques avec un aminoindole associe a un derive quinonique. |
| DE4017516A1 (de) | 1990-05-31 | 1991-12-05 | Wella Ag | Oxidationshaarfaerbemittel mit einem gehalt an 3-aminophenol-derivaten, verfahren zum oxidativen faerben von haaren sowie neue 3-aminophenol-derivate |
| DE4026530A1 (de) | 1990-08-22 | 1992-02-27 | Basf Ag | Synergistische mittel zur regulierung des pflanzenwachstums |
| US5175151A (en) | 1990-09-07 | 1992-12-29 | Schering Corporation | Antiviral compounds and antihypertensive compounds |
| WO1992004327A1 (en) | 1990-09-07 | 1992-03-19 | Schering Corporation | Antiviral compounds and antihypertensive compounds |
| CA2091173A1 (en) | 1990-09-07 | 1992-03-08 | Adriano Afonso | Antiviral compounds and antihypertensive compounds |
| JPH04171521A (ja) | 1990-11-05 | 1992-06-18 | Fujitsu Ltd | タッチパネル |
| IL100917A0 (en) | 1991-02-16 | 1992-11-15 | Fisons Plc | Pyridinone and pyrimidinone derivatives,their preparation and pharmaceutical compositions containing them |
| CA2065106A1 (en) | 1991-04-04 | 1992-10-05 | Junichi Fukawa | Silver halide photographic light-sensitive material and photographic product for film-making process |
| FR2675380A1 (fr) | 1991-04-18 | 1992-10-23 | Oreal | Procede de teinture des fibres keratiniques avec des aminoindoles, a ph basique, compositions mises en óoeuvre et nouveaux composes. |
| GB9108547D0 (en) | 1991-04-22 | 1991-06-05 | Fujisawa Pharmaceutical Co | Quinoline derivatives |
| CA2075154A1 (en) | 1991-08-06 | 1993-02-07 | Neelakantan Balasubramanian | Peptide aldehydes as antithrombotic agents |
| JPH05345780A (ja) | 1991-12-24 | 1993-12-27 | Kumiai Chem Ind Co Ltd | ピリミジンまたはトリアジン誘導体及び除草剤 |
| AU668181B2 (en) | 1992-05-20 | 1996-04-26 | Merck & Co., Inc. | Ester derivatives of 4-aza-steroids |
| EP0641204B1 (en) | 1992-05-20 | 2000-08-16 | Merck & Co. Inc. | 17-ethers and thioethers of 4-aza-steroids |
| US5352690A (en) | 1992-07-01 | 1994-10-04 | Eli Lilly And Company | 1,2,4-trioxygenated benzene derivatives useful as leukotriene antagonists |
| JP2718830B2 (ja) | 1992-07-10 | 1998-02-25 | ラボラトワール、グラクソ、ソシエテ、アノニム | アニリド誘導体 |
| US5322847A (en) | 1992-11-05 | 1994-06-21 | Pfizer Inc. | Azabenzimidazoles in the treatment of asthma, arthritis and related diseases |
| WO1994014797A1 (en) | 1992-12-23 | 1994-07-07 | Smithkline Beecham Corporation | Quinoline compounds and the treatment of leucotriene related diseases therewith |
| US5750754A (en) | 1993-03-29 | 1998-05-12 | Zeneca Limited | Heterocyclic compounds |
| JP3760474B2 (ja) | 1993-04-22 | 2006-03-29 | ダイキン工業株式会社 | 電気エネルギーを発生させる方法、装置およびそれに用いるn−f結合を有する化合物 |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| GB9420590D0 (en) | 1993-10-22 | 1994-11-30 | Zeneca Ltd | Pyridazino quinoline compounds |
| WO1995023153A1 (en) | 1994-02-25 | 1995-08-31 | Laboratorios Aranda, S.A. De C.V. | Quinolonylcarboxamidocephalosporin derivatives and pharmaceutical compositions containing them |
| FR2720397B1 (fr) | 1994-05-24 | 1996-08-23 | Laphal Laboratoires Sa | Nouveaux oxathiolanes, leur procédé de préparation et les compositions pharmaceutiques qui en renferment. |
| SK282721B6 (sk) | 1994-05-27 | 2002-11-06 | Smithkline Beecham S.P.A. | Nepeptidové NK3 antagonistické látky, spôsob ich výroby, farmaceutické prostriedky s ich obsahom a ich použitie |
| EP0705835A1 (de) | 1994-09-01 | 1996-04-10 | Ciba-Geigy Ag | Oxa- oder thiaaliphatisch überbrückte Chinoxalin-2,3-dione |
| AU1106195A (en) | 1994-11-09 | 1996-06-06 | Novo Nordisk A/S | Heterocyclic compounds, their preparation and use |
| GB9501567D0 (en) | 1995-01-26 | 1995-03-15 | Pharmacia Spa | Hydrosoluble 3-arylidene-2-oxindole derivatives as tyrosine kinase inhibitors |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| DE19601142A1 (de) | 1995-07-13 | 1997-01-16 | Agfa Gevaert Ag | Verfahren zur Erzeugung eines farbigen Bildes |
| EP0841929B1 (en) | 1995-08-02 | 2003-05-07 | Darwin Discovery Limited | Quinolones and their therapeutic use |
| DE69631423T2 (de) | 1995-08-02 | 2004-12-02 | Darwin Discovery Ltd., Slough | Chinolone und deren therapeutische verwendung |
| DE19532235A1 (de) | 1995-08-31 | 1997-03-06 | Keppler Bernhard K Priv Doz Dr | An Phosphonsäuren gekoppelte antibakteriell wirksame Verbindungen zur Therapie von Infektionen im Bereich des Knochens |
| EP0876349B1 (en) | 1995-10-19 | 2002-09-11 | Takeda Chemical Industries, Ltd. | Quinoline derivatives as gnrh antagonists |
| AU710825B2 (en) | 1996-02-21 | 1999-09-30 | Darwin Discovery Limited | Quinolones and their therapeutic use |
| US6215016B1 (en) | 1996-03-27 | 2001-04-10 | Toray Industries, Inc. | Ketone derivatives and medical application thereof |
| DE19615262A1 (de) | 1996-04-18 | 1997-10-23 | Bayer Ag | Heteroverknüpfte Phenylglycinolamide |
| EP0952832B1 (en) | 1996-05-20 | 2008-08-27 | Darwin Discovery Limited | Quinoline carboxamides as tnf inhibitors and as pde-iv inhibitors |
| US5834485A (en) | 1996-05-20 | 1998-11-10 | Chiroscience Limited | Quinoline sulfonamides and their therapeutic use |
| KR20000022040A (ko) | 1996-06-20 | 2000-04-25 | 보오드 오브 리젠츠, 더 유니버시티 오브 텍사스 시스템 | 약학적 활성 제제를 제공하기 위한 화합물, 방법 및 그의 용도 |
| ES2197354T3 (es) | 1996-07-23 | 2004-01-01 | Neurogen Corporation | Derivados de bencilamina sustituidos con amido y amino; una nueva clase de ligandos especificos del neuropeptido y1. |
| GB9717576D0 (en) | 1997-08-19 | 1997-10-22 | Xenova Ltd | Pharmaceutical compounds |
| US6069151A (en) | 1996-11-06 | 2000-05-30 | Darwin Discovery, Ltd. | Quinolines and their therapeutic use |
| DE19651099A1 (de) | 1996-12-09 | 1998-06-10 | Consortium Elektrochem Ind | Mehrkomponentensystem zum Verändern, Abbau oder Bleichen von Lignin, ligninhaltigen Materialien oder ähnlichen Stoffen sowie Verfahren zu seiner Anwendung |
| WO1998031226A1 (de) | 1997-01-15 | 1998-07-23 | Novartis Ag | Herbizides mittel |
| ZA986594B (en) | 1997-07-25 | 1999-01-27 | Abbott Lab | Urokinase inhibitors |
| US6258822B1 (en) | 1997-08-06 | 2001-07-10 | Abbott Laboratories | Urokinase inhibitors |
| US6429207B1 (en) | 1997-11-21 | 2002-08-06 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| CA2315646C (en) | 1997-12-22 | 2010-02-09 | Bayer Corporation | Inhibition of raf kinase using symmetrical and unsymmetrical substituted diphenyl ureas |
| DE19818614A1 (de) | 1998-04-20 | 1999-10-21 | Basf Ag | Neue substituierte Amide, deren Herstellung und Anwendung |
| US6444617B1 (en) | 1998-07-28 | 2002-09-03 | Nihon Nohyaku Co., Ltd. | Fused-heterocycle dicarboxylic acid diamide derivatives or salts thereof, herbicide and usage thereof |
| CN1128148C (zh) | 1998-08-03 | 2003-11-19 | 应用研究系统Ars股份公司 | (1H)-苯并[c]喹嗪-3-酮衍生物的合成方法 |
| FR2786483B1 (fr) | 1998-12-01 | 2001-02-16 | Rhodia Chimie Sa | Procede de preparation de 4-hydroxyquinoleines et/ou formes tautomeres |
| JP2000256358A (ja) | 1999-03-10 | 2000-09-19 | Yamanouchi Pharmaceut Co Ltd | ピラゾール誘導体 |
| CA2371472A1 (en) | 1999-05-06 | 2000-11-16 | Neurogen Corporation | Substituted 4-oxo-quinoline-3-carboxamides: gaba brain receptor ligands |
| SE0002320D0 (sv) | 1999-10-25 | 2000-06-21 | Active Biotech Ab | Malignant tumors |
| CN100390148C (zh) | 1999-10-25 | 2008-05-28 | 活跃生物技术有限公司 | 用于治疗恶性肿瘤的药物 |
| DE60024861T2 (de) | 1999-10-28 | 2006-07-06 | Trine Pharmaceuticals, Inc., Waltham | Pumpeninhibitoren zur freisetzung von medikamenten |
| WO2001034570A1 (en) | 1999-11-08 | 2001-05-17 | Sankyo Company, Limited | Nitrogenous heterocycle derivatives |
| UA75055C2 (uk) | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| GT200000203A (es) | 1999-12-01 | 2002-05-24 | Compuestos, composiciones y metodos para estimular el crecimiento y elongacion de neuronas. | |
| JP2001233859A (ja) | 2000-02-23 | 2001-08-28 | Yamanouchi Pharmaceut Co Ltd | 抗ヘリコバクター・ヒ゜ロリ化合物の新規製造法及びその中間体 |
| GB0011409D0 (en) | 2000-05-11 | 2000-06-28 | Smithkline Beecham Plc | Novel compounds |
| AU2001268691A1 (en) | 2000-06-29 | 2002-01-21 | Clairol Incorporated | Iodo-containing organic couplers for use in oxidative hair dyeing |
| HUP0302825A3 (en) | 2000-07-13 | 2005-02-28 | Takeda Pharmaceutical | Lipid-rich plaque inhibitors |
| AU2001277731A1 (en) | 2000-08-09 | 2002-02-18 | Welfide Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| JP2002212179A (ja) | 2001-01-15 | 2002-07-31 | Wakunaga Pharmaceut Co Ltd | 新規アニリド誘導体又はその塩及びこれを含有する医薬 |
| GB2372986A (en) | 2001-01-17 | 2002-09-11 | Xenova Ltd | 2-oxo, 4-hydroxy pyrroles and quinolines |
| GB0102687D0 (en) | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
| TWI243164B (en) | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
| DE10108271A1 (de) | 2001-02-21 | 2002-08-22 | Schering Ag | Chinolin-, Isochinolin- und Phthalazinderivate als Antagonisten des Gonadotropin freisetzenden Hormons |
| US6515001B2 (en) | 2001-03-05 | 2003-02-04 | Chemokine Therapeutic Corporation | IL-8 receptor ligands-drugs for inflammatory and autoimmune diseases |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
| KR100894189B1 (ko) | 2001-03-29 | 2009-04-22 | 일라이 릴리 앤드 캄파니 | 5-ht6 수용체의 길항제로서의 n-(2-아릴에틸)벤질아민 |
| US6878713B2 (en) | 2001-04-25 | 2005-04-12 | Wockhardt Limited | Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments |
| JP2002322054A (ja) | 2001-04-26 | 2002-11-08 | Dai Ichi Seiyaku Co Ltd | 薬剤排出ポンプ阻害薬 |
| JP2002322154A (ja) | 2001-04-27 | 2002-11-08 | Dai Ichi Seiyaku Co Ltd | 抗真菌化合物 |
| WO2002094809A1 (fr) | 2001-05-24 | 2002-11-28 | Yamanouchi Pharmaceutical Co., Ltd. | Derives de 3-quinoleine-2-(1h)-ylideneindoline-2-one |
| JP4164028B2 (ja) | 2001-10-12 | 2008-10-08 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | アルキンマトリックスメタロプロテイナーゼ阻害剤 |
| JP2005519876A (ja) | 2001-11-27 | 2005-07-07 | メルク エンド カムパニー インコーポレーテッド | 2−アミノキノリン化合物 |
| CA2468544A1 (en) | 2001-12-10 | 2003-06-19 | Amgen Inc. | Vanilloid receptor ligands |
| JP2003238413A (ja) | 2002-02-14 | 2003-08-27 | Kyowa Hakko Kogyo Co Ltd | ステロイドスルファターゼ阻害剤 |
| DE10211413A1 (de) | 2002-03-15 | 2003-09-25 | Wella Ag | Quinolinium-Salze enthaltende Färbemittel |
| US6930131B2 (en) | 2002-04-10 | 2005-08-16 | Wyeth | Aryl substituted 3-ethoxy phenyl trifluoromethane sulfonamides for the treatment of non-insulin dependent diabetes mellitus (NIDDM) |
| US7037913B2 (en) | 2002-05-01 | 2006-05-02 | Bristol-Myers Squibb Company | Bicyclo 4.4.0 antiviral derivatives |
| EP1503759B1 (en) | 2002-05-14 | 2008-12-17 | The Regents Of The University Of California | Substituted quinolone carboxylic acids, their derivatives, site of action, and uses thereof |
| EP1506188B1 (en) | 2002-05-14 | 2009-02-25 | Xenova Limited | Process for the preparation of a hydrate of an anthranilic acid derivative |
| AU2003251944B2 (en) | 2002-07-15 | 2008-06-26 | Myriad Genetics, Inc. | Compounds, compositions, and methods employing same |
| US20040033959A1 (en) | 2002-07-19 | 2004-02-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Pharmaceutical compositions for hepatitis C viral protease inhibitors |
| EP1539163A1 (en) | 2002-08-13 | 2005-06-15 | Warner-Lambert Company LLC | 4-hydroxyquinoline derivatives as matrix metalloproteinase inhibitors |
| TWI314041B (en) | 2002-10-21 | 2009-09-01 | Sankyo Agro Co Ltd | Quinolyl-3-carboxamide compound |
| WO2004105779A2 (en) | 2003-05-27 | 2004-12-09 | Cesare Montecucco | Green tea and oplyphenol inhibitors of bacterial proteases |
| WO2005009971A1 (ja) | 2003-07-24 | 2005-02-03 | Astellas Pharma Inc. | キノロン誘導体又はその塩 |
| US7598412B2 (en) | 2003-10-08 | 2009-10-06 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| NZ587549A (en) * | 2004-06-24 | 2012-10-26 | Vertex Pharma | 6-Amino-indole derivatives and processes for their preparation |
| US8354427B2 (en) * | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| US7804769B1 (en) * | 2005-12-01 | 2010-09-28 | Juniper Networks, Inc. | Non-stop forwarding in a multi-chassis router |
| WO2007067559A2 (en) | 2005-12-06 | 2007-06-14 | Regents Of The University Of Minnesota | Antibacterial agents |
| MX2008008320A (es) * | 2005-12-23 | 2008-09-03 | Smithkline Beecham Corp | Inhibidores de azaindol de aurora cinasas. |
| KR101578235B1 (ko) | 2007-12-10 | 2015-12-16 | 노파르티스 아게 | 유기 화합물 |
| US20110257223A1 (en) * | 2008-10-23 | 2011-10-20 | Vertex Pharmaceuticals Incorporated | Modulators of Cystic Fibrosis Transmembrane Conductance Regulator |
-
2009
- 2009-12-11 US US12/635,927 patent/US8354427B2/en active Active
-
2010
- 2010-12-10 WO PCT/US2010/059920 patent/WO2011072241A1/en not_active Ceased
- 2010-12-10 EP EP10793116A patent/EP2509954A1/en not_active Withdrawn
- 2010-12-10 NZ NZ600707A patent/NZ600707A/en unknown
- 2010-12-10 CA CA2783314A patent/CA2783314A1/en not_active Abandoned
- 2010-12-10 JP JP2012543310A patent/JP2013513617A/ja active Pending
- 2010-12-10 AU AU2010327993A patent/AU2010327993A1/en not_active Abandoned
- 2010-12-10 RU RU2012129206/04A patent/RU2552353C2/ru active
- 2010-12-10 MX MX2012006764A patent/MX2012006764A/es active IP Right Grant
- 2010-12-10 CN CN201080056022XA patent/CN102652128A/zh active Pending
-
2012
- 2012-06-10 IL IL220283A patent/IL220283A0/en unknown
- 2012-11-30 US US13/690,924 patent/US8614327B2/en not_active Expired - Lifetime
-
2015
- 2015-07-06 BE BE2015C040C patent/BE2015C040I2/nl unknown
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